# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 #TrackingRef '- acrispinirevised.CIF' _publ_contact_author_name 'Crispini, Alessandra' _publ_contact_author_address ; Dipartimento di Scienze Farmaceutiche Universit\'a della Calabria 87030 Arcavacata di Rende (CS) Italy ; _publ_contact_author_email a.crispini@unical.it _publ_contact_author_fax 0984492066 _publ_contact_author_phone 0984492888 _publ_requested_coeditor_name ? _publ_contact_letter ; Please consider this CIF submission for publication as a Comunication in Dalton Transactions ; _publ_requested_category SC _publ_section_title ; Luminescence Mechanochromism in Cyclometallated Ir(III) Complexes Containing Picolinamine. ; _publ_section_title_footnote ; ? ; loop_ _publ_author_name _publ_author_address T.Mastropietro ; Dipartimento di Chimica Universit\'a della Calabria 87030 Arcavacata di Rende (CS) Italy ; Y.Yadev ; Dipartimento di Chimica Universit\'a della Calabria 87030 Arcavacata di Rende (CS) Italy ; E.I.Szerb ; Dipartimento di Chimica Universit\'a della Calabria 87030 Arcavacata di Rende (CS) Italy ; A.M.Talarico ; Dipartimento di Chimica Universit\'a della Calabria 87030 Arcavacata di Rende (CS) Italy ; M.Ghedini ; Dipartimento di Chimica Universit\'a della Calabria 87030 Arcavacata di Rende (CS) Italy ; ; A.Crispini ; ; Dipartimento di Scienze Farmaceutiche Universit\'a della Calabria 87030 Arcavacata di Rende (CS) Italy ; data_(1a) _database_code_depnum_ccdc_archive 'CCDC 873662' #TrackingRef '- acrispinirevised.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H24 Ir N4, C2 H6 O, Cl' _chemical_formula_sum 'C30 H30 Cl Ir N4 O' _chemical_formula_weight 690.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.2312(13) _cell_length_b 11.7771(11) _cell_length_c 19.2326(18) _cell_angle_alpha 90.00 _cell_angle_beta 104.770(4) _cell_angle_gamma 90.00 _cell_volume 3116.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7152 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 31.02 _exptl_crystal_description parallelepiped _exptl_crystal_colour yellow _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.471 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 4.396 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8163 _exptl_absorpt_correction_T_max 0.9328 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 91356 _diffrn_reflns_av_R_equivalents 0.0504 _diffrn_reflns_av_sigmaI/netI 0.0323 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 26.00 _reflns_number_total 6109 _reflns_number_gt 4668 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker-Nonius X8 APEX' _computing_cell_refinement 'Bruker-Nonius X8 APEX' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0860P)^2^+7.6815P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6109 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0654 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.1746 _refine_ls_wR_factor_gt 0.1377 _refine_ls_goodness_of_fit_ref 1.258 _refine_ls_restrained_S_all 1.258 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.765023(17) 0.75061(2) 0.314982(15) 0.04416(15) Uani 1 1 d . . . N1 N 0.6964(4) 0.9096(6) 0.3086(3) 0.0516(15) Uani 1 1 d . . . C1 C 0.7302(6) 1.0058(7) 0.2871(5) 0.062(2) Uani 1 1 d . . . H1 H 0.7913 1.0057 0.2779 0.075 Uiso 1 1 calc R . . C2 C 0.6763(7) 1.1065(9) 0.2780(6) 0.082(3) Uani 1 1 d . . . H2 H 0.7017 1.1723 0.2633 0.098 Uiso 1 1 calc R . . C3 C 0.5839(7) 1.1080(9) 0.2911(6) 0.088(3) Uani 1 1 d . . . H3 H 0.5464 1.1737 0.2843 0.105 Uiso 1 1 calc R . . C4 C 0.5502(6) 1.0078(9) 0.3145(6) 0.078(3) Uani 1 1 d . . . H4 H 0.4894 1.0068 0.3242 0.093 Uiso 1 1 calc R . . C5 C 0.6063(5) 0.9080(7) 0.3238(5) 0.0569(19) Uani 1 1 d . . . C6 C 0.5783(5) 0.7977(8) 0.3484(5) 0.0571(19) Uani 1 1 d . . . C7 C 0.4933(7) 0.7791(11) 0.3717(6) 0.078(3) Uani 1 1 d . . . H7 H 0.4509 0.8391 0.3718 0.094 Uiso 1 1 calc R . . C8 C 0.4725(7) 0.6752(12) 0.3939(6) 0.089(3) Uani 1 1 d . . . H8 H 0.4161 0.6647 0.4091 0.106 Uiso 1 1 calc R . . C9 C 0.5347(8) 0.5841(9) 0.3943(6) 0.083(3) Uani 1 1 d . . . H9 H 0.5193 0.5133 0.4099 0.099 Uiso 1 1 calc R . . C10 C 0.6220(7) 0.5974(9) 0.3711(5) 0.075(3) Uani 1 1 d . . . H10 H 0.6627 0.5356 0.3710 0.090 Uiso 1 1 calc R . . C11 C 0.6461(5) 0.7058(8) 0.3482(5) 0.0538(18) Uani 1 1 d . . . N2 N 0.8154(4) 0.5862(5) 0.3154(4) 0.0518(15) Uani 1 1 d . . . C12 C 0.8720(6) 0.5316(7) 0.3728(5) 0.063(2) Uani 1 1 d . . . H12 H 0.8917 0.5706 0.4162 0.076 Uiso 1 1 calc R . . C13 C 0.9021(7) 0.4198(8) 0.3699(7) 0.082(3) Uani 1 1 d . . . H13 H 0.9418 0.3863 0.4108 0.098 Uiso 1 1 calc R . . C14 C 0.8739(8) 0.3584(8) 0.3075(8) 0.089(3) Uani 1 1 d . . . H14 H 0.8930 0.2833 0.3051 0.106 Uiso 1 1 calc R . . C15 C 0.8149(7) 0.4137(8) 0.2472(6) 0.080(3) Uani 1 1 d . . . H15 H 0.7947 0.3744 0.2040 0.096 Uiso 1 1 calc R . . C16 C 0.7852(5) 0.5300(7) 0.2509(5) 0.056(2) Uani 1 1 d . . . C17 C 0.7201(5) 0.5972(7) 0.1928(4) 0.0558(19) Uani 1 1 d . . . C18 C 0.6819(6) 0.5543(9) 0.1207(5) 0.072(3) Uani 1 1 d . . . H18 H 0.6990 0.4823 0.1083 0.086 Uiso 1 1 calc R . . C19 C 0.6200(8) 0.6210(13) 0.0708(6) 0.093(4) Uani 1 1 d . . . H19 H 0.5950 0.5945 0.0242 0.112 Uiso 1 1 calc R . . C20 C 0.5953(9) 0.7257(12) 0.0897(7) 0.087(3) Uani 1 1 d . . . H20 H 0.5528 0.7697 0.0555 0.104 Uiso 1 1 calc R . . C21 C 0.6315(8) 0.7699(9) 0.1587(6) 0.075(3) Uani 1 1 d . . . H21 H 0.6130 0.8423 0.1693 0.090 Uiso 1 1 calc R . . C22 C 0.6966(5) 0.7051(8) 0.2133(4) 0.0529(18) Uani 1 1 d . . . N3 N 0.9026(4) 0.8050(5) 0.2896(3) 0.0454(13) Uani 1 1 d . . . H3B H 0.9158 0.7584 0.2562 0.054 Uiso 1 1 calc R . . H3A H 0.8957 0.8759 0.2715 0.054 Uiso 1 1 calc R . . C23 C 0.9840(5) 0.8019(8) 0.3558(4) 0.0578(19) Uani 1 1 d . . . H23B H 1.0306 0.8605 0.3527 0.069 Uiso 1 1 calc R . . H23A H 1.0167 0.7291 0.3585 0.069 Uiso 1 1 calc R . . N4 N 0.8558(4) 0.7989(6) 0.4197(3) 0.0498(14) Uani 1 1 d . . . C24 C 0.9509(5) 0.8192(6) 0.4231(4) 0.0476(16) Uani 1 1 d . . . C25 C 1.0163(6) 0.8501(7) 0.4885(5) 0.065(2) Uani 1 1 d . . . H25 H 1.0816 0.8613 0.4904 0.078 Uiso 1 1 calc R . . C26 C 0.9843(8) 0.8636(8) 0.5494(5) 0.079(3) Uani 1 1 d . . . H26 H 1.0273 0.8844 0.5926 0.095 Uiso 1 1 calc R . . C27 C 0.8858(8) 0.8457(9) 0.5456(5) 0.082(3) Uani 1 1 d . . . H27 H 0.8620 0.8560 0.5859 0.098 Uiso 1 1 calc R . . C28 C 0.8242(6) 0.8121(9) 0.4802(5) 0.068(2) Uani 1 1 d . . . H28 H 0.7591 0.7982 0.4779 0.082 Uiso 1 1 calc R . . Cl1 Cl 0.96519(14) 1.08134(17) 0.25941(12) 0.0597(5) Uani 1 1 d . . . O1 O 0.7962(8) 1.1199(11) 0.1245(6) 0.080(4) Uani 0.50 1 d P . . H1A H 0.8416 1.1160 0.1606 0.096 Uiso 0.50 1 calc PR . . C29 C 0.7647(14) 1.0054(19) 0.0999(12) 0.080(5) Uani 0.50 1 d P . . H29A H 0.7633 0.9558 0.1399 0.096 Uiso 0.50 1 calc PR . . H29B H 0.7009 1.0063 0.0663 0.096 Uiso 0.50 1 calc PR . . C30 C 0.826(3) 0.977(4) 0.0712(16) 0.179(19) Uani 0.50 1 d P . . H30A H 0.8124 0.9017 0.0528 0.269 Uiso 0.50 1 calc PR . . H30B H 0.8879 0.9791 0.1054 0.269 Uiso 0.50 1 calc PR . . H30C H 0.8258 1.0285 0.0324 0.269 Uiso 0.50 1 calc PR . . O2 O 0.2372(8) 0.8152(11) 0.4496(6) 0.068(3) Uani 0.50 1 d P . . H2A H 0.2340 0.7516 0.4320 0.103 Uiso 0.50 1 calc PR . . C31 C 0.3113(13) 0.8177(18) 0.5141(10) 0.073(5) Uani 0.50 1 d P . . H31A H 0.2992 0.8809 0.5429 0.088 Uiso 0.50 1 calc PR . . H31B H 0.3727 0.8321 0.5025 0.088 Uiso 0.50 1 calc PR . . C32 C 0.3214(19) 0.714(2) 0.5579(12) 0.089(7) Uani 0.50 1 d P . . H32A H 0.3734 0.7238 0.6005 0.133 Uiso 0.50 1 calc PR . . H32B H 0.3355 0.6511 0.5306 0.133 Uiso 0.50 1 calc PR . . H32C H 0.2619 0.7001 0.5713 0.133 Uiso 0.50 1 calc PR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.0382(2) 0.0465(2) 0.0513(2) 0.00354(11) 0.01794(14) 0.00281(9) N1 0.038(3) 0.056(4) 0.065(4) -0.002(3) 0.019(3) 0.011(2) C1 0.055(4) 0.055(5) 0.083(6) 0.016(4) 0.028(4) 0.005(4) C2 0.078(6) 0.060(6) 0.116(9) 0.017(5) 0.039(5) 0.020(4) C3 0.078(6) 0.060(6) 0.128(10) -0.005(6) 0.031(6) 0.028(5) C4 0.047(4) 0.089(7) 0.100(7) -0.006(6) 0.025(4) 0.020(4) C5 0.041(3) 0.065(5) 0.068(5) -0.002(4) 0.020(3) 0.010(3) C6 0.040(4) 0.066(5) 0.067(5) -0.008(4) 0.018(3) -0.002(4) C7 0.050(5) 0.098(8) 0.094(8) -0.008(6) 0.031(5) -0.006(5) C8 0.060(5) 0.116(10) 0.102(8) -0.006(7) 0.044(5) -0.021(6) C9 0.093(7) 0.069(6) 0.095(8) 0.016(5) 0.041(6) -0.026(5) C10 0.067(5) 0.080(6) 0.085(7) 0.012(5) 0.033(5) -0.017(5) C11 0.041(4) 0.061(5) 0.063(5) 0.004(4) 0.021(3) -0.011(3) N2 0.048(3) 0.045(3) 0.069(4) 0.008(3) 0.028(3) 0.001(3) C12 0.067(5) 0.049(4) 0.079(6) 0.011(4) 0.028(4) 0.006(4) C13 0.080(6) 0.058(6) 0.114(9) 0.025(6) 0.035(6) 0.021(5) C14 0.094(7) 0.036(4) 0.153(11) 0.002(6) 0.064(7) 0.006(4) C15 0.080(6) 0.062(6) 0.116(9) -0.024(6) 0.058(6) -0.017(5) C16 0.052(4) 0.048(4) 0.081(6) -0.009(4) 0.040(4) -0.010(3) C17 0.049(4) 0.061(5) 0.064(5) -0.006(4) 0.027(3) -0.017(3) C18 0.069(5) 0.076(6) 0.082(7) -0.027(5) 0.043(5) -0.027(5) C19 0.076(6) 0.142(12) 0.060(6) -0.013(7) 0.013(5) -0.043(7) C20 0.075(7) 0.109(9) 0.070(7) 0.001(6) 0.005(5) -0.015(6) C21 0.060(5) 0.090(7) 0.071(7) 0.009(5) 0.009(5) -0.001(4) C22 0.039(3) 0.066(5) 0.056(5) -0.001(4) 0.016(3) -0.011(3) N3 0.042(3) 0.040(3) 0.058(4) -0.003(3) 0.020(2) -0.004(2) C23 0.039(3) 0.073(5) 0.064(5) -0.003(4) 0.017(3) 0.005(3) N4 0.048(3) 0.051(4) 0.052(4) 0.001(3) 0.016(3) 0.009(3) C24 0.048(3) 0.037(3) 0.059(5) 0.000(3) 0.016(3) 0.010(3) C25 0.069(5) 0.052(5) 0.068(6) -0.003(4) 0.006(4) 0.011(4) C26 0.101(7) 0.066(6) 0.060(6) -0.004(4) 0.002(5) 0.015(5) C27 0.098(7) 0.089(7) 0.062(6) -0.011(5) 0.026(5) 0.029(6) C28 0.065(5) 0.076(6) 0.067(6) -0.002(5) 0.024(4) 0.017(4) Cl1 0.0649(11) 0.0487(10) 0.0724(13) 0.0021(9) 0.0302(9) -0.0009(8) O1 0.071(7) 0.083(9) 0.066(8) 0.016(7) -0.018(6) -0.023(6) C29 0.065(11) 0.087(14) 0.088(15) -0.005(12) 0.018(10) 0.008(10) C30 0.16(3) 0.25(5) 0.10(2) -0.08(3) -0.014(19) 0.09(3) O2 0.074(7) 0.056(7) 0.064(7) 0.017(6) -0.003(5) -0.008(5) C31 0.067(10) 0.076(12) 0.070(12) 0.013(10) 0.004(8) 0.004(9) C32 0.115(17) 0.066(12) 0.071(14) -0.009(10) 0.000(12) -0.007(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 C22 2.022(8) . ? Ir1 C11 2.026(7) . ? Ir1 N2 2.065(6) . ? Ir1 N1 2.101(6) . ? Ir1 N4 2.174(6) . ? Ir1 N3 2.229(5) . ? N1 C1 1.336(10) . ? N1 C5 1.386(9) . ? C1 C2 1.400(12) . ? C1 H1 0.9300 . ? C2 C3 1.399(13) . ? C2 H2 0.9300 . ? C3 C4 1.392(14) . ? C3 H3 0.9300 . ? C4 C5 1.407(12) . ? C4 H4 0.9300 . ? C5 C6 1.472(13) . ? C6 C7 1.410(12) . ? C6 C11 1.450(13) . ? C7 C8 1.353(17) . ? C7 H7 0.9300 . ? C8 C9 1.389(16) . ? C8 H8 0.9300 . ? C9 C10 1.433(13) . ? C9 H9 0.9300 . ? C10 C11 1.421(13) . ? C10 H10 0.9300 . ? N2 C12 1.352(10) . ? N2 C16 1.376(10) . ? C12 C13 1.390(12) . ? C12 H12 0.9300 . ? C13 C14 1.371(16) . ? C13 H13 0.9300 . ? C14 C15 1.406(16) . ? C14 H14 0.9300 . ? C15 C16 1.440(12) . ? C15 H15 0.9300 . ? C16 C17 1.485(12) . ? C17 C22 1.397(12) . ? C17 C18 1.444(12) . ? C18 C19 1.373(16) . ? C18 H18 0.9300 . ? C19 C20 1.357(17) . ? C19 H19 0.9300 . ? C20 C21 1.396(17) . ? C20 H20 0.9300 . ? C21 C22 1.431(13) . ? C21 H21 0.9300 . ? N3 C23 1.488(9) . ? N3 H3B 0.9000 . ? N3 H3A 0.9000 . ? C23 C24 1.501(11) . ? C23 H23B 0.9700 . ? C23 H23A 0.9700 . ? N4 C24 1.359(9) . ? N4 C28 1.359(11) . ? C24 C25 1.408(11) . ? C25 C26 1.370(13) . ? C25 H25 0.9300 . ? C26 C27 1.400(14) . ? C26 H26 0.9300 . ? C27 C28 1.395(13) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? O1 C29 1.46(2) . ? O1 H1A 0.8200 . ? C29 C30 1.19(3) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? O2 C31 1.41(2) . ? O2 H2A 0.8200 . ? C31 C32 1.47(3) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C22 Ir1 C11 90.0(3) . . ? C22 Ir1 N2 80.6(3) . . ? C11 Ir1 N2 94.1(3) . . ? C22 Ir1 N1 94.4(3) . . ? C11 Ir1 N1 80.6(3) . . ? N2 Ir1 N1 172.8(2) . . ? C22 Ir1 N4 172.6(2) . . ? C11 Ir1 N4 97.1(3) . . ? N2 Ir1 N4 96.7(3) . . ? N1 Ir1 N4 88.8(2) . . ? C22 Ir1 N3 95.6(2) . . ? C11 Ir1 N3 174.4(3) . . ? N2 Ir1 N3 87.0(2) . . ? N1 Ir1 N3 98.7(2) . . ? N4 Ir1 N3 77.3(2) . . ? C1 N1 C5 120.1(7) . . ? C1 N1 Ir1 125.1(5) . . ? C5 N1 Ir1 114.6(5) . . ? N1 C1 C2 121.9(8) . . ? N1 C1 H1 119.1 . . ? C2 C1 H1 119.1 . . ? C3 C2 C1 119.9(9) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C4 C3 C2 117.7(8) . . ? C4 C3 H3 121.2 . . ? C2 C3 H3 121.2 . . ? C3 C4 C5 121.2(8) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? N1 C5 C4 119.2(8) . . ? N1 C5 C6 114.9(7) . . ? C4 C5 C6 125.9(7) . . ? C7 C6 C11 120.7(9) . . ? C7 C6 C5 124.3(9) . . ? C11 C6 C5 115.0(7) . . ? C8 C7 C6 121.0(11) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C7 C8 C9 120.7(9) . . ? C7 C8 H8 119.7 . . ? C9 C8 H8 119.7 . . ? C8 C9 C10 121.0(10) . . ? C8 C9 H9 119.5 . . ? C10 C9 H9 119.5 . . ? C11 C10 C9 119.4(9) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C10 C11 C6 117.2(7) . . ? C10 C11 Ir1 128.2(7) . . ? C6 C11 Ir1 114.6(6) . . ? C12 N2 C16 119.5(7) . . ? C12 N2 Ir1 125.7(6) . . ? C16 N2 Ir1 114.8(5) . . ? N2 C12 C13 122.9(9) . . ? N2 C12 H12 118.6 . . ? C13 C12 H12 118.6 . . ? C14 C13 C12 120.7(10) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 117.3(9) . . ? C13 C14 H14 121.4 . . ? C15 C14 H14 121.4 . . ? C14 C15 C16 121.4(10) . . ? C14 C15 H15 119.3 . . ? C16 C15 H15 119.3 . . ? N2 C16 C15 118.3(9) . . ? N2 C16 C17 114.5(7) . . ? C15 C16 C17 127.2(9) . . ? C22 C17 C18 122.1(8) . . ? C22 C17 C16 114.9(7) . . ? C18 C17 C16 123.0(8) . . ? C19 C18 C17 119.2(10) . . ? C19 C18 H18 120.4 . . ? C17 C18 H18 120.4 . . ? C20 C19 C18 119.8(10) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C19 C20 C21 122.4(12) . . ? C19 C20 H20 118.8 . . ? C21 C20 H20 118.8 . . ? C20 C21 C22 120.8(11) . . ? C20 C21 H21 119.6 . . ? C22 C21 H21 119.6 . . ? C17 C22 C21 115.8(8) . . ? C17 C22 Ir1 115.1(6) . . ? C21 C22 Ir1 129.1(7) . . ? C23 N3 Ir1 109.9(4) . . ? C23 N3 H3B 109.7 . . ? Ir1 N3 H3B 109.7 . . ? C23 N3 H3A 109.7 . . ? Ir1 N3 H3A 109.7 . . ? H3B N3 H3A 108.2 . . ? N3 C23 C24 112.9(6) . . ? N3 C23 H23B 109.0 . . ? C24 C23 H23B 109.0 . . ? N3 C23 H23A 109.0 . . ? C24 C23 H23A 109.0 . . ? H23B C23 H23A 107.8 . . ? C24 N4 C28 118.8(7) . . ? C24 N4 Ir1 116.1(5) . . ? C28 N4 Ir1 125.1(5) . . ? N4 C24 C25 120.8(7) . . ? N4 C24 C23 117.5(6) . . ? C25 C24 C23 121.6(7) . . ? C26 C25 C24 120.3(8) . . ? C26 C25 H25 119.8 . . ? C24 C25 H25 119.8 . . ? C25 C26 C27 119.0(9) . . ? C25 C26 H26 120.5 . . ? C27 C26 H26 120.5 . . ? C28 C27 C26 118.7(9) . . ? C28 C27 H27 120.6 . . ? C26 C27 H27 120.6 . . ? N4 C28 C27 122.3(8) . . ? N4 C28 H28 118.8 . . ? C27 C28 H28 118.8 . . ? C29 O1 H1A 109.5 . . ? C30 C29 O1 102(3) . . ? C30 C29 H29A 111.4 . . ? O1 C29 H29A 111.4 . . ? C30 C29 H29B 111.4 . . ? O1 C29 H29B 111.4 . . ? H29A C29 H29B 109.2 . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C31 O2 H2A 109.5 . . ? O2 C31 C32 115.5(16) . . ? O2 C31 H31A 108.4 . . ? C32 C31 H31A 108.4 . . ? O2 C31 H31B 108.4 . . ? C32 C31 H31B 108.4 . . ? H31A C31 H31B 107.5 . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.337 _refine_diff_density_min -2.756 _refine_diff_density_rms 0.600 #===END data_(1b) _database_code_depnum_ccdc_archive 'CCDC 873663' #TrackingRef '- acrispinirevised.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H24 Ir N4, Cl' _chemical_formula_sum 'C28 H24 Cl Ir N4' _chemical_formula_weight 644.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 9.8167(17) _cell_length_b 13.747(3) _cell_length_c 20.447(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2759.3(9) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 60 _cell_measurement_theta_min 4.381 _cell_measurement_theta_max 30.635 _exptl_crystal_description parallelepiped _exptl_crystal_colour orange _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.551 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1256 _exptl_absorpt_coefficient_mu 4.957 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.601 _exptl_absorpt_correction_T_max 0.762 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17671 _diffrn_reflns_av_R_equivalents 0.0811 _diffrn_reflns_av_sigmaI/netI 0.0691 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4749 _reflns_number_gt 4315 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0812P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.023(17) _refine_ls_number_reflns 4749 _refine_ls_number_parameters 295 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0487 _refine_ls_R_factor_gt 0.0429 _refine_ls_wR_factor_ref 0.1055 _refine_ls_wR_factor_gt 0.1017 _refine_ls_goodness_of_fit_ref 0.859 _refine_ls_restrained_S_all 0.859 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.42862(3) 0.11725(2) 0.193029(15) 0.03468(12) Uani 1 1 d . . . Cl1 Cl 0.7104(4) 0.9583(2) 0.03168(18) 0.0761(9) Uani 1 1 d . . . N1 N 0.4154(9) 0.1829(5) 0.1033(4) 0.0446(18) Uani 1 1 d . . . C1 C 0.4630(11) 0.1482(9) 0.0485(5) 0.056(3) Uani 1 1 d . . . H1 H 0.5152 0.0917 0.0496 0.067 Uiso 1 1 calc R . . C2 C 0.4377(16) 0.1937(10) -0.0130(6) 0.073(3) Uani 1 1 d . . . H2 H 0.4691 0.1661 -0.0518 0.087 Uiso 1 1 calc R . . C3 C 0.3673(15) 0.2775(10) -0.0134(7) 0.069(4) Uani 1 1 d . . . H3 H 0.3506 0.3098 -0.0525 0.083 Uiso 1 1 calc R . . C4 C 0.3213(12) 0.3142(9) 0.0433(6) 0.060(3) Uani 1 1 d . . . H4 H 0.2737 0.3727 0.0424 0.072 Uiso 1 1 calc R . . C5 C 0.3411(10) 0.2693(8) 0.1026(6) 0.050(3) Uani 1 1 d . . . C6 C 0.2947(11) 0.2997(7) 0.1669(6) 0.047(2) Uani 1 1 d . . . C7 C 0.2150(12) 0.3838(8) 0.1776(6) 0.063(3) Uani 1 1 d . . . H7 H 0.1899 0.4228 0.1424 0.076 Uiso 1 1 calc R . . C8 C 0.1746(12) 0.4080(9) 0.2396(8) 0.069(4) Uani 1 1 d . . . H8 H 0.1213 0.4630 0.2463 0.083 Uiso 1 1 calc R . . C9 C 0.2120(12) 0.3517(8) 0.2918(6) 0.063(3) Uani 1 1 d . . . H9 H 0.1836 0.3688 0.3337 0.076 Uiso 1 1 calc R . . C10 C 0.2930(12) 0.2681(8) 0.2830(5) 0.051(2) Uani 1 1 d . . . H10 H 0.3219 0.2319 0.3188 0.061 Uiso 1 1 calc R . . C11 C 0.3296(9) 0.2402(7) 0.2189(5) 0.043(2) Uani 1 1 d . . . N2 N 0.4440(7) 0.0652(4) 0.2856(2) 0.050(2) Uani 1 1 d G . . C12 C 0.3454(7) 0.0096(5) 0.3169(4) 0.068(3) Uani 1 1 d G . . H12 H 0.2671 -0.0090 0.2946 0.082 Uiso 1 1 calc R . . C13 C 0.3638(10) -0.0181(7) 0.3817(4) 0.089(5) Uani 1 1 d G . . H13 H 0.2978 -0.0553 0.4027 0.106 Uiso 1 1 calc R . . C14 C 0.4808(11) 0.0097(7) 0.4151(3) 0.100(6) Uani 1 1 d G . . H14 H 0.4931 -0.0089 0.4584 0.120 Uiso 1 1 calc R . . C15 C 0.5794(9) 0.0653(6) 0.3837(3) 0.074(4) Uani 1 1 d G . . H15 H 0.6577 0.0839 0.4061 0.089 Uiso 1 1 calc R . . C16 C 0.5610(7) 0.0931(4) 0.3190(3) 0.049(3) Uani 1 1 d G . . C17 C 0.6540(10) 0.1511(7) 0.2795(5) 0.048(2) Uani 1 1 d . . . C18 C 0.7826(13) 0.1806(10) 0.3057(8) 0.073(3) Uani 1 1 d . . . H18 H 0.8114 0.1630 0.3474 0.087 Uiso 1 1 calc R . . C19 C 0.8626(14) 0.2386(12) 0.2634(10) 0.087(5) Uani 1 1 d . . . H19 H 0.9467 0.2605 0.2783 0.104 Uiso 1 1 calc R . . C20 C 0.8222(13) 0.2641(10) 0.2020(8) 0.075(4) Uani 1 1 d . . . H20 H 0.8793 0.3001 0.1749 0.090 Uiso 1 1 calc R . . C21 C 0.6936(11) 0.2349(8) 0.1805(7) 0.062(3) Uani 1 1 d . . . H21 H 0.6625 0.2558 0.1399 0.074 Uiso 1 1 calc R . . C22 C 0.6102(10) 0.1751(7) 0.2187(5) 0.047(2) Uani 1 1 d . . . N3 N 0.5180(10) -0.0210(6) 0.1599(4) 0.048(2) Uani 1 1 d . . . H3B H 0.5612 -0.0116 0.1216 0.058 Uiso 1 1 calc R . . H3A H 0.5798 -0.0414 0.1894 0.058 Uiso 1 1 calc R . . C23 C 0.4132(13) -0.0953(7) 0.1518(7) 0.068(3) Uani 1 1 d . . . H23B H 0.4083 -0.1347 0.1911 0.081 Uiso 1 1 calc R . . H23A H 0.4378 -0.1376 0.1157 0.081 Uiso 1 1 calc R . . C24 C 0.2772(11) -0.0515(7) 0.1387(5) 0.046(2) Uani 1 1 d . . . N4 N 0.2512(8) 0.0360(5) 0.1644(4) 0.0401(18) Uani 1 1 d . . . C25 C 0.1756(13) -0.1036(9) 0.1060(6) 0.066(3) Uani 1 1 d . . . H25 H 0.1938 -0.1651 0.0892 0.079 Uiso 1 1 calc R . . C26 C 0.0435(12) -0.0611(10) 0.0987(6) 0.062(3) Uani 1 1 d . . . H26 H -0.0262 -0.0932 0.0766 0.075 Uiso 1 1 calc R . . C27 C 0.0255(12) 0.0247(10) 0.1244(7) 0.070(4) Uani 1 1 d . . . H27 H -0.0587 0.0548 0.1191 0.084 Uiso 1 1 calc R . . C28 C 0.1262(12) 0.0737(9) 0.1595(7) 0.067(3) Uani 1 1 d . . . H28 H 0.1063 0.1327 0.1796 0.080 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.03197(18) 0.03900(16) 0.03308(18) 0.00242(13) -0.00373(15) 0.00189(14) Cl1 0.0618(19) 0.089(2) 0.078(2) 0.0127(16) 0.0240(17) 0.0081(16) N1 0.033(4) 0.047(4) 0.054(5) -0.002(3) -0.008(4) 0.003(4) C1 0.051(7) 0.076(7) 0.042(6) 0.009(5) 0.003(5) 0.011(5) C2 0.084(9) 0.096(9) 0.037(6) 0.008(5) -0.005(6) -0.012(9) C3 0.070(8) 0.085(9) 0.052(8) 0.036(6) -0.020(6) -0.006(7) C4 0.055(7) 0.061(6) 0.063(8) 0.023(5) -0.019(6) -0.007(5) C5 0.026(5) 0.065(6) 0.060(7) 0.010(5) -0.006(4) -0.002(4) C6 0.034(5) 0.041(5) 0.066(7) 0.003(4) -0.010(5) 0.000(4) C7 0.061(6) 0.039(4) 0.090(9) -0.003(5) 0.003(6) -0.001(5) C8 0.048(7) 0.055(7) 0.105(11) -0.018(7) 0.004(7) 0.006(5) C9 0.050(6) 0.060(6) 0.079(9) -0.024(6) 0.018(6) -0.004(5) C10 0.048(6) 0.056(5) 0.048(6) -0.015(4) 0.002(5) -0.004(5) C11 0.024(5) 0.046(5) 0.060(6) -0.011(4) -0.005(4) -0.003(4) N2 0.067(6) 0.049(4) 0.034(4) -0.001(3) -0.002(4) 0.002(4) C12 0.090(9) 0.072(7) 0.043(7) 0.010(5) 0.002(6) -0.009(6) C13 0.147(15) 0.078(8) 0.041(7) 0.013(6) 0.022(9) -0.005(9) C14 0.161(17) 0.097(10) 0.043(8) 0.000(7) -0.024(10) 0.054(11) C15 0.103(11) 0.070(7) 0.048(7) -0.002(5) -0.008(8) 0.020(8) C16 0.080(7) 0.026(4) 0.042(6) -0.007(3) -0.023(5) 0.024(4) C17 0.040(5) 0.056(5) 0.049(6) -0.015(4) 0.002(4) 0.005(4) C18 0.046(6) 0.094(8) 0.079(8) -0.019(8) -0.025(7) 0.012(6) C19 0.036(7) 0.105(11) 0.119(14) -0.061(10) -0.017(8) 0.003(7) C20 0.048(7) 0.088(8) 0.088(11) -0.029(8) 0.009(7) -0.017(6) C21 0.047(7) 0.056(6) 0.081(9) -0.003(5) -0.005(6) -0.002(5) C22 0.034(5) 0.054(5) 0.054(6) -0.015(4) -0.004(4) 0.006(4) N3 0.061(6) 0.048(4) 0.036(4) -0.002(3) -0.007(4) 0.015(4) C23 0.068(8) 0.046(5) 0.089(9) -0.001(5) 0.005(7) -0.010(5) C24 0.033(5) 0.052(5) 0.053(6) 0.008(4) -0.003(4) -0.005(4) N4 0.034(5) 0.044(4) 0.042(4) 0.007(3) 0.003(3) -0.003(3) C25 0.071(8) 0.067(7) 0.061(7) -0.009(5) 0.003(6) -0.024(6) C26 0.047(7) 0.089(9) 0.050(7) 0.024(6) -0.011(5) -0.031(6) C27 0.039(7) 0.076(8) 0.095(10) 0.027(7) -0.022(6) -0.014(6) C28 0.039(6) 0.066(6) 0.095(9) 0.038(6) 0.007(6) 0.012(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 C11 2.020(9) . ? Ir1 C22 2.021(9) . ? Ir1 N2 2.028(5) . ? Ir1 N1 2.049(8) . ? Ir1 N4 2.150(8) . ? Ir1 N3 2.200(8) . ? N1 C1 1.304(13) . ? N1 C5 1.394(13) . ? C1 C2 1.427(16) . ? C1 H1 0.9300 . ? C2 C3 1.34(2) . ? C2 H2 0.9300 . ? C3 C4 1.34(2) . ? C3 H3 0.9300 . ? C4 C5 1.375(16) . ? C4 H4 0.9300 . ? C5 C6 1.453(17) . ? C6 C11 1.384(15) . ? C6 C7 1.413(15) . ? C7 C8 1.370(19) . ? C7 H7 0.9300 . ? C8 C9 1.37(2) . ? C8 H8 0.9300 . ? C9 C10 1.409(16) . ? C9 H9 0.9300 . ? C10 C11 1.413(14) . ? C10 H10 0.9300 . ? N2 C12 1.3900 . ? N2 C16 1.3900 . ? C12 C13 1.3900 . ? C12 H12 0.9300 . ? C13 C14 1.3900 . ? C13 H13 0.9300 . ? C14 C15 1.3900 . ? C14 H14 0.9300 . ? C15 C16 1.3900 . ? C15 H15 0.9300 . ? C16 C17 1.457(13) . ? C17 C22 1.355(15) . ? C17 C18 1.430(16) . ? C18 C19 1.41(2) . ? C18 H18 0.9300 . ? C19 C20 1.36(2) . ? C19 H19 0.9300 . ? C20 C21 1.396(17) . ? C20 H20 0.9300 . ? C21 C22 1.399(16) . ? C21 H21 0.9300 . ? N3 C23 1.460(14) . ? N3 H3B 0.9000 . ? N3 H3A 0.9000 . ? C23 C24 1.489(17) . ? C23 H23B 0.9700 . ? C23 H23A 0.9700 . ? C24 N4 1.336(13) . ? C24 C25 1.398(16) . ? N4 C28 1.336(14) . ? C25 C26 1.430(18) . ? C25 H25 0.9300 . ? C26 C27 1.30(2) . ? C26 H26 0.9300 . ? C27 C28 1.395(19) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 Ir1 C22 91.6(4) . . ? C11 Ir1 N2 95.0(4) . . ? C22 Ir1 N2 80.2(4) . . ? C11 Ir1 N1 80.5(4) . . ? C22 Ir1 N1 96.6(4) . . ? N2 Ir1 N1 174.5(3) . . ? C11 Ir1 N4 96.7(3) . . ? C22 Ir1 N4 171.6(3) . . ? N2 Ir1 N4 97.5(3) . . ? N1 Ir1 N4 86.2(3) . . ? C11 Ir1 N3 174.4(4) . . ? C22 Ir1 N3 93.9(4) . . ? N2 Ir1 N3 87.3(3) . . ? N1 Ir1 N3 97.5(3) . . ? N4 Ir1 N3 77.9(3) . . ? C1 N1 C5 119.4(9) . . ? C1 N1 Ir1 125.8(7) . . ? C5 N1 Ir1 114.7(7) . . ? N1 C1 C2 122.3(11) . . ? N1 C1 H1 118.8 . . ? C2 C1 H1 118.8 . . ? C3 C2 C1 118.0(12) . . ? C3 C2 H2 121.0 . . ? C1 C2 H2 121.0 . . ? C4 C3 C2 119.4(10) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C3 C4 C5 123.0(11) . . ? C3 C4 H4 118.5 . . ? C5 C4 H4 118.5 . . ? C4 C5 N1 117.7(11) . . ? C4 C5 C6 128.7(10) . . ? N1 C5 C6 113.6(9) . . ? C11 C6 C7 120.2(10) . . ? C11 C6 C5 116.5(9) . . ? C7 C6 C5 123.3(10) . . ? C8 C7 C6 120.1(11) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C9 C8 C7 120.5(10) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C8 C9 C10 120.8(11) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C9 C10 C11 119.0(11) . . ? C9 C10 H10 120.5 . . ? C11 C10 H10 120.5 . . ? C6 C11 C10 119.3(9) . . ? C6 C11 Ir1 114.4(8) . . ? C10 C11 Ir1 126.3(8) . . ? C12 N2 C16 120.0 . . ? C12 N2 Ir1 124.9(3) . . ? C16 N2 Ir1 115.0(3) . . ? C13 C12 N2 120.0 . . ? C13 C12 H12 120.0 . . ? N2 C12 H12 120.0 . . ? C12 C13 C14 120.0 . . ? C12 C13 H13 120.0 . . ? C14 C13 H13 120.0 . . ? C13 C14 C15 120.0 . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C16 C15 C14 120.0 . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 N2 120.0 . . ? C15 C16 C17 126.6(6) . . ? N2 C16 C17 113.4(6) . . ? C22 C17 C18 123.7(11) . . ? C22 C17 C16 116.2(9) . . ? C18 C17 C16 120.1(10) . . ? C19 C18 C17 114.9(13) . . ? C19 C18 H18 122.5 . . ? C17 C18 H18 122.5 . . ? C20 C19 C18 123.1(12) . . ? C20 C19 H19 118.4 . . ? C18 C19 H19 118.4 . . ? C19 C20 C21 118.6(14) . . ? C19 C20 H20 120.7 . . ? C21 C20 H20 120.7 . . ? C20 C21 C22 121.5(13) . . ? C20 C21 H21 119.3 . . ? C22 C21 H21 119.3 . . ? C17 C22 C21 118.0(10) . . ? C17 C22 Ir1 115.0(8) . . ? C21 C22 Ir1 127.0(8) . . ? C23 N3 Ir1 111.0(7) . . ? C23 N3 H3B 109.4 . . ? Ir1 N3 H3B 109.4 . . ? C23 N3 H3A 109.4 . . ? Ir1 N3 H3A 109.4 . . ? H3B N3 H3A 108.0 . . ? N3 C23 C24 111.6(8) . . ? N3 C23 H23B 109.3 . . ? C24 C23 H23B 109.3 . . ? N3 C23 H23A 109.3 . . ? C24 C23 H23A 109.3 . . ? H23B C23 H23A 108.0 . . ? N4 C24 C25 120.9(10) . . ? N4 C24 C23 117.7(9) . . ? C25 C24 C23 121.2(10) . . ? C28 N4 C24 119.7(10) . . ? C28 N4 Ir1 124.3(8) . . ? C24 N4 Ir1 114.8(7) . . ? C24 C25 C26 119.2(11) . . ? C24 C25 H25 120.4 . . ? C26 C25 H25 120.4 . . ? C27 C26 C25 116.7(11) . . ? C27 C26 H26 121.6 . . ? C25 C26 H26 121.6 . . ? C26 C27 C28 123.2(12) . . ? C26 C27 H27 118.4 . . ? C28 C27 H27 118.4 . . ? N4 C28 C27 120.2(13) . . ? N4 C28 H28 119.9 . . ? C27 C28 H28 119.9 . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 2.796 _refine_diff_density_min -1.021 _refine_diff_density_rms 0.155 #===END data_(2) _database_code_depnum_ccdc_archive 'CCDC 873664' #TrackingRef '- acrispinirevised.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H24 Ir N4, F6 P' _chemical_formula_sum 'C28 H24 F6 Ir N4 P' _chemical_formula_weight 753.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c a 21' _symmetry_space_group_name_Hall 'P 2c -2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 11.0809(13) _cell_length_b 15.5306(18) _cell_length_c 16.1226(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2774.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 123 _cell_measurement_theta_min 4.528 _cell_measurement_theta_max 54.183 _exptl_crystal_description parallelepiped _exptl_crystal_colour orange _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.804 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1464 _exptl_absorpt_coefficient_mu 4.935 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.698 _exptl_absorpt_correction_T_max 0.723 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 94838 _diffrn_reflns_av_R_equivalents 0.0473 _diffrn_reflns_av_sigmaI/netI 0.0189 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.31 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4876 _reflns_number_gt 4664 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0627P)^2^+0.6647P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.087(8) _refine_ls_number_reflns 4876 _refine_ls_number_parameters 358 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0289 _refine_ls_R_factor_gt 0.0261 _refine_ls_wR_factor_ref 0.0855 _refine_ls_wR_factor_gt 0.0751 _refine_ls_goodness_of_fit_ref 1.170 _refine_ls_restrained_S_all 1.169 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.046747(12) 0.231895(8) 0.25172(3) 0.03299(9) Uani 1 1 d . . . C1 C 0.2699(5) 0.2006(4) 0.1428(4) 0.0487(13) Uani 1 1 d . . . H1 H 0.2660 0.2595 0.1324 0.058 Uiso 1 1 calc R . . C22 C -0.0823(5) 0.2053(4) 0.1646(3) 0.0394(10) Uani 1 1 d . . . N1 N 0.1844(4) 0.1646(3) 0.1938(3) 0.0386(9) Uani 1 1 d . . . C11 C 0.0188(5) 0.1109(4) 0.2973(3) 0.0402(11) Uani 1 1 d . . . C21 C -0.0720(5) 0.1606(4) 0.0900(4) 0.0448(12) Uani 1 1 d . . . H21 H 0.0022 0.1372 0.0752 0.054 Uiso 1 1 calc R . . C18 C -0.2974(7) 0.2285(5) 0.1309(5) 0.0599(19) Uani 1 1 d . . . H18 H -0.3722 0.2517 0.1445 0.072 Uiso 1 1 calc R . . C19 C -0.2827(7) 0.1825(5) 0.0579(4) 0.0669(18) Uani 1 1 d . . . H19 H -0.3485 0.1735 0.0231 0.080 Uiso 1 1 calc R . . C14 C -0.3073(7) 0.3618(5) 0.3769(5) 0.0663(18) Uani 1 1 d . . . H14 H -0.3767 0.3855 0.4000 0.080 Uiso 1 1 calc R . . C6 C 0.0977(5) 0.0476(3) 0.2683(3) 0.0429(14) Uani 1 1 d . . . C17 C -0.1984(6) 0.2397(4) 0.1837(4) 0.0434(13) Uani 1 1 d . . . C16 C -0.2079(5) 0.2856(4) 0.2644(5) 0.0484(16) Uani 1 1 d . . . N2 N -0.1015(4) 0.2878(3) 0.3086(3) 0.0404(10) Uani 1 1 d . . . C15 C -0.3113(6) 0.3245(5) 0.2969(5) 0.0631(16) Uani 1 1 d . . . H15 H -0.3823 0.3258 0.2661 0.076 Uiso 1 1 calc R . . C12 C -0.0998(6) 0.3252(4) 0.3849(4) 0.0492(13) Uani 1 1 d . . . H12 H -0.0278 0.3254 0.4146 0.059 Uiso 1 1 calc R . . C5 C 0.1917(5) 0.0776(4) 0.2099(4) 0.0425(11) Uani 1 1 d . . . N4 N 0.1813(5) 0.2765(3) 0.3395(3) 0.0424(12) Uani 1 1 d . . . C7 C 0.0874(7) -0.0395(4) 0.2932(4) 0.0569(14) Uani 1 1 d . . . H7 H 0.1403 -0.0805 0.2721 0.068 Uiso 1 1 calc R . . C9 C -0.0806(8) -0.0012(5) 0.3814(4) 0.0686(18) Uani 1 1 d . . . H9 H -0.1387 -0.0169 0.4202 0.082 Uiso 1 1 calc R . . C4 C 0.2815(6) 0.0274(4) 0.1728(4) 0.0595(15) Uani 1 1 d . . . H4 H 0.2835 -0.0316 0.1827 0.071 Uiso 1 1 calc R . . C3 C 0.3671(6) 0.0639(5) 0.1218(5) 0.0630(17) Uani 1 1 d . . . H3 H 0.4273 0.0300 0.0983 0.076 Uiso 1 1 calc R . . C8 C -0.0018(8) -0.0639(4) 0.3492(5) 0.0675(18) Uani 1 1 d . . . H8 H -0.0093 -0.1212 0.3652 0.081 Uiso 1 1 calc R . . C2 C 0.3629(5) 0.1528(5) 0.1055(5) 0.0611(17) Uani 1 1 d . . . H2 H 0.4197 0.1790 0.0714 0.073 Uiso 1 1 calc R . . C13 C -0.2005(6) 0.3630(5) 0.4203(4) 0.0605(16) Uani 1 1 d . . . H13 H -0.1960 0.3886 0.4723 0.073 Uiso 1 1 calc R . . C20 C -0.1715(7) 0.1500(5) 0.0367(4) 0.0612(16) Uani 1 1 d . . . H20 H -0.1619 0.1208 -0.0133 0.073 Uiso 1 1 calc R . . C10 C -0.0724(6) 0.0847(5) 0.3554(4) 0.0549(14) Uani 1 1 d . . . H10 H -0.1264 0.1251 0.3761 0.066 Uiso 1 1 calc R . . C23 C 0.1418(6) 0.4161(4) 0.2733(4) 0.0555(18) Uani 1 1 d . . . H23A H 0.0771 0.4445 0.3032 0.067 Uiso 1 1 calc R . . H23B H 0.1933 0.4602 0.2496 0.067 Uiso 1 1 calc R . . N3 N 0.0904(5) 0.3622(3) 0.2060(3) 0.0481(11) Uani 1 1 d . . . H3A H 0.1440 0.3583 0.1642 0.058 Uiso 1 1 calc R . . H3B H 0.0231 0.3872 0.1862 0.058 Uiso 1 1 calc R . . C24 C 0.2140(5) 0.3615(4) 0.3323(4) 0.0493(13) Uani 1 1 d . . . C25 C 0.3093(7) 0.3972(6) 0.3803(5) 0.074(2) Uani 1 1 d . . . H25 H 0.3321 0.4545 0.3737 0.089 Uiso 1 1 calc R . . C26 C 0.3681(6) 0.3440(8) 0.4376(5) 0.078(3) Uani 1 1 d . . . H26 H 0.4284 0.3660 0.4717 0.094 Uiso 1 1 calc R . . C27 C 0.3348(7) 0.2577(7) 0.4428(5) 0.075(2) Uani 1 1 d . . . H27 H 0.3758 0.2212 0.4789 0.090 Uiso 1 1 calc R . . C28 C 0.2425(7) 0.2261(4) 0.3954(5) 0.0559(17) Uani 1 1 d . . . H28 H 0.2205 0.1686 0.4012 0.067 Uiso 1 1 calc R . . F5 F 0.0725(7) 0.4755(6) 0.4961(6) 0.141(3) Uani 1 1 d . . . F4 F 0.2183(4) 0.4246(4) 0.5831(4) 0.0894(14) Uani 1 1 d . . . F3 F 0.0459(4) 0.3524(4) 0.5582(4) 0.0904(17) Uani 1 1 d . . . P1 P 0.0779(4) 0.4525(3) 0.5829(4) 0.0468(12) Uiso 0.530(15) 1 d P A 1 F2 F -0.0631(7) 0.4744(7) 0.5878(7) 0.072(3) Uiso 0.530(15) 1 d P A 1 F1 F 0.1079(9) 0.5510(7) 0.6005(7) 0.091(3) Uiso 0.530(15) 1 d P A 1 F6 F 0.0742(12) 0.4411(11) 0.6831(8) 0.105(4) Uiso 0.530(15) 1 d P A 1 F1A F 0.1152(11) 0.5253(9) 0.6514(9) 0.094(4) Uiso 0.470(15) 1 d P A 2 P1A P 0.0756(4) 0.4397(4) 0.6029(4) 0.0483(14) Uiso 0.470(15) 1 d P A 2 F2A F -0.0619(9) 0.4514(8) 0.6235(9) 0.073(3) Uiso 0.470(15) 1 d P A 2 F6A F 0.0881(11) 0.3869(9) 0.6835(7) 0.082(3) Uiso 0.470(15) 1 d P A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.03173(13) 0.02886(13) 0.03838(13) -0.00044(15) -0.00057(12) 0.00188(5) C1 0.036(3) 0.043(3) 0.067(4) 0.002(3) 0.009(3) 0.006(3) C22 0.040(3) 0.034(2) 0.044(3) 0.003(2) -0.002(2) -0.006(3) N1 0.034(2) 0.034(2) 0.047(2) 0.0026(18) -0.0007(18) 0.0026(18) C11 0.040(3) 0.042(3) 0.039(3) 0.003(2) -0.006(2) -0.008(2) C21 0.047(3) 0.046(3) 0.041(3) -0.003(3) 0.004(2) -0.009(3) C18 0.043(4) 0.082(6) 0.055(4) -0.002(3) -0.011(3) 0.002(3) C19 0.057(4) 0.087(5) 0.057(4) -0.001(3) -0.019(3) -0.003(4) C14 0.054(4) 0.063(4) 0.082(5) -0.014(4) 0.014(3) 0.007(3) C6 0.042(3) 0.037(2) 0.050(4) 0.004(2) -0.009(2) 0.000(2) C17 0.042(3) 0.048(3) 0.040(3) 0.002(2) -0.010(2) 0.002(2) C16 0.040(3) 0.046(2) 0.059(5) -0.004(3) -0.001(3) 0.010(2) N2 0.034(2) 0.038(2) 0.050(3) -0.007(2) 0.002(2) 0.001(2) C15 0.047(3) 0.065(4) 0.077(4) -0.010(4) -0.008(3) 0.011(3) C12 0.048(3) 0.053(3) 0.047(3) -0.012(3) -0.001(2) 0.003(3) C5 0.042(3) 0.038(3) 0.048(3) -0.001(2) -0.004(2) 0.005(2) N4 0.036(2) 0.046(3) 0.045(3) -0.0078(19) -0.005(2) 0.0101(19) C7 0.057(4) 0.047(3) 0.067(4) 0.010(3) -0.002(3) 0.003(3) C9 0.079(4) 0.067(4) 0.060(4) 0.018(4) 0.018(4) -0.017(4) C4 0.063(4) 0.040(3) 0.076(4) 0.004(3) 0.014(3) 0.013(3) C3 0.048(3) 0.057(4) 0.084(5) -0.007(3) 0.020(3) 0.014(3) C8 0.074(5) 0.050(4) 0.079(5) 0.024(3) 0.001(4) -0.006(4) C2 0.047(3) 0.053(3) 0.083(4) -0.008(3) 0.021(3) 0.002(3) C13 0.064(4) 0.060(4) 0.057(3) -0.010(3) 0.010(3) 0.003(3) C20 0.072(4) 0.073(4) 0.039(3) -0.004(3) -0.005(3) -0.016(4) C10 0.054(3) 0.057(4) 0.054(4) 0.005(3) 0.007(3) -0.003(3) C23 0.058(3) 0.033(3) 0.075(5) -0.002(2) 0.004(3) -0.003(2) N3 0.045(3) 0.035(2) 0.064(3) 0.007(2) 0.004(2) 0.007(2) C24 0.040(3) 0.051(3) 0.056(3) -0.015(3) 0.005(2) -0.006(2) C25 0.047(4) 0.094(6) 0.081(5) -0.030(5) 0.008(3) -0.020(4) C26 0.038(3) 0.130(9) 0.067(4) -0.038(5) -0.004(3) -0.008(4) C27 0.047(4) 0.126(7) 0.052(4) -0.011(4) -0.008(4) 0.025(4) C28 0.053(4) 0.056(4) 0.059(4) 0.002(3) -0.003(3) 0.017(3) F5 0.124(5) 0.149(7) 0.151(6) 0.077(6) -0.016(4) -0.006(5) F4 0.044(2) 0.108(4) 0.116(4) -0.025(3) 0.000(2) 0.009(2) F3 0.091(4) 0.063(3) 0.118(5) -0.008(3) -0.022(3) 0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 C11 2.041(5) . ? Ir1 C22 2.046(6) . ? Ir1 N1 2.072(4) . ? Ir1 N2 2.072(5) . ? Ir1 N4 2.170(5) . ? Ir1 N3 2.207(5) . ? C1 N1 1.373(8) . ? C1 C2 1.406(9) . ? C1 H1 0.9300 . ? C22 C21 1.394(8) . ? C22 C17 1.427(9) . ? N1 C5 1.378(7) . ? C11 C6 1.396(8) . ? C11 C10 1.437(9) . ? C21 C20 1.408(9) . ? C21 H21 0.9300 . ? C18 C19 1.387(11) . ? C18 C17 1.400(10) . ? C18 H18 0.9300 . ? C19 C20 1.375(11) . ? C19 H19 0.9300 . ? C14 C13 1.376(11) . ? C14 C15 1.415(11) . ? C14 H14 0.9300 . ? C6 C7 1.416(8) . ? C6 C5 1.479(8) . ? C17 C16 1.487(9) . ? C16 N2 1.378(8) . ? C16 C15 1.397(9) . ? N2 C12 1.361(7) . ? C15 H15 0.9300 . ? C12 C13 1.383(9) . ? C12 H12 0.9300 . ? C5 C4 1.399(8) . ? N4 C24 1.373(8) . ? N4 C28 1.374(9) . ? C7 C8 1.390(11) . ? C7 H7 0.9300 . ? C9 C10 1.401(11) . ? C9 C8 1.407(12) . ? C9 H9 0.9300 . ? C4 C3 1.378(10) . ? C4 H4 0.9300 . ? C3 C2 1.405(11) . ? C3 H3 0.9300 . ? C8 H8 0.9300 . ? C2 H2 0.9300 . ? C13 H13 0.9300 . ? C20 H20 0.9300 . ? C10 H10 0.9300 . ? C23 N3 1.485(8) . ? C23 C24 1.504(9) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? N3 H3A 0.9000 . ? N3 H3B 0.9000 . ? C24 C25 1.423(9) . ? C25 C26 1.401(14) . ? C25 H25 0.9300 . ? C26 C27 1.393(14) . ? C26 H26 0.9300 . ? C27 C28 1.368(12) . ? C27 H27 0.9300 . ? C28 H28 0.9300 . ? F5 P1 1.445(10) . ? F5 P1A 1.809(11) . ? F4 P1 1.614(6) . ? F4 P1A 1.630(6) . ? F3 P1A 1.570(7) . ? F3 P1 1.643(6) . ? P1 F1 1.591(11) . ? P1 F2 1.602(9) . ? P1 F6 1.625(14) . ? F1A P1A 1.604(14) . ? P1A F6A 1.543(13) . ? P1A F2A 1.570(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 Ir1 C22 87.4(2) . . ? C11 Ir1 N1 79.0(2) . . ? C22 Ir1 N1 95.9(2) . . ? C11 Ir1 N2 96.1(2) . . ? C22 Ir1 N2 80.4(2) . . ? N1 Ir1 N2 174.13(18) . . ? C11 Ir1 N4 99.4(2) . . ? C22 Ir1 N4 172.9(2) . . ? N1 Ir1 N4 87.09(18) . . ? N2 Ir1 N4 97.0(2) . . ? C11 Ir1 N3 175.84(19) . . ? C22 Ir1 N3 96.3(2) . . ? N1 Ir1 N3 98.64(18) . . ? N2 Ir1 N3 86.4(2) . . ? N4 Ir1 N3 76.96(19) . . ? N1 C1 C2 123.1(6) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C21 C22 C17 116.6(5) . . ? C21 C22 Ir1 129.4(5) . . ? C17 C22 Ir1 114.0(4) . . ? C1 N1 C5 118.2(5) . . ? C1 N1 Ir1 124.9(4) . . ? C5 N1 Ir1 116.9(4) . . ? C6 C11 C10 117.3(6) . . ? C6 C11 Ir1 115.6(4) . . ? C10 C11 Ir1 127.0(5) . . ? C22 C21 C20 121.4(6) . . ? C22 C21 H21 119.3 . . ? C20 C21 H21 119.3 . . ? C19 C18 C17 119.3(7) . . ? C19 C18 H18 120.4 . . ? C17 C18 H18 120.4 . . ? C20 C19 C18 120.4(6) . . ? C20 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C13 C14 C15 119.7(6) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C11 C6 C7 121.8(6) . . ? C11 C6 C5 115.6(5) . . ? C7 C6 C5 122.6(5) . . ? C18 C17 C22 121.9(6) . . ? C18 C17 C16 122.5(6) . . ? C22 C17 C16 115.6(5) . . ? N2 C16 C15 119.8(6) . . ? N2 C16 C17 113.8(5) . . ? C15 C16 C17 126.4(6) . . ? C12 N2 C16 119.3(5) . . ? C12 N2 Ir1 124.6(4) . . ? C16 N2 Ir1 116.1(4) . . ? C16 C15 C14 119.6(6) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? N2 C12 C13 122.9(6) . . ? N2 C12 H12 118.6 . . ? C13 C12 H12 118.6 . . ? N1 C5 C4 120.5(5) . . ? N1 C5 C6 112.8(5) . . ? C4 C5 C6 126.7(5) . . ? C24 N4 C28 118.3(6) . . ? C24 N4 Ir1 115.6(4) . . ? C28 N4 Ir1 125.8(4) . . ? C8 C7 C6 120.1(7) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C10 C9 C8 120.5(6) . . ? C10 C9 H9 119.7 . . ? C8 C9 H9 119.7 . . ? C3 C4 C5 121.1(6) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C4 C3 C2 119.5(6) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C7 C8 C9 119.5(6) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? C3 C2 C1 117.7(6) . . ? C3 C2 H2 121.2 . . ? C1 C2 H2 121.2 . . ? C14 C13 C12 118.6(6) . . ? C14 C13 H13 120.7 . . ? C12 C13 H13 120.7 . . ? C19 C20 C21 120.5(6) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C9 C10 C11 120.7(7) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? N3 C23 C24 110.3(5) . . ? N3 C23 H23A 109.6 . . ? C24 C23 H23A 109.6 . . ? N3 C23 H23B 109.6 . . ? C24 C23 H23B 109.6 . . ? H23A C23 H23B 108.1 . . ? C23 N3 Ir1 110.9(4) . . ? C23 N3 H3A 109.5 . . ? Ir1 N3 H3A 109.5 . . ? C23 N3 H3B 109.5 . . ? Ir1 N3 H3B 109.5 . . ? H3A N3 H3B 108.0 . . ? N4 C24 C25 121.7(7) . . ? N4 C24 C23 117.1(5) . . ? C25 C24 C23 121.2(6) . . ? C26 C25 C24 118.2(8) . . ? C26 C25 H25 120.9 . . ? C24 C25 H25 120.9 . . ? C27 C26 C25 119.0(7) . . ? C27 C26 H26 120.5 . . ? C25 C26 H26 120.5 . . ? C28 C27 C26 120.6(8) . . ? C28 C27 H27 119.7 . . ? C26 C27 H27 119.7 . . ? C27 C28 N4 122.1(7) . . ? C27 C28 H28 119.0 . . ? N4 C28 H28 119.0 . . ? P1 F5 P1A 3.8(3) . . ? P1 F4 P1A 13.4(2) . . ? P1A F3 P1 13.3(2) . . ? F5 P1 F1 86.8(6) . . ? F5 P1 F2 87.4(6) . . ? F1 P1 F2 89.5(5) . . ? F5 P1 F4 96.2(5) . . ? F1 P1 F4 93.2(5) . . ? F2 P1 F4 175.6(6) . . ? F5 P1 F6 171.0(8) . . ? F1 P1 F6 86.1(7) . . ? F2 P1 F6 87.1(7) . . ? F4 P1 F6 89.7(6) . . ? F5 P1 F3 89.5(5) . . ? F1 P1 F3 176.2(6) . . ? F2 P1 F3 90.1(4) . . ? F4 P1 F3 87.4(3) . . ? F6 P1 F3 97.6(6) . . ? F6A P1A F2A 88.3(7) . . ? F6A P1A F3 86.9(6) . . ? F2A P1A F3 89.6(5) . . ? F6A P1A F1A 90.3(7) . . ? F2A P1A F1A 93.8(6) . . ? F3 P1A F1A 175.5(6) . . ? F6A P1A F4 90.1(6) . . ? F2A P1A F4 178.1(7) . . ? F3 P1A F4 89.4(3) . . ? F1A P1A F4 87.1(5) . . ? F6A P1A F5 165.1(6) . . ? F2A P1A F5 98.5(6) . . ? F3 P1A F5 79.9(5) . . ? F1A P1A F5 102.4(6) . . ? F4 P1A F5 82.9(5) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 2.299 _refine_diff_density_min -0.684 _refine_diff_density_rms 0.191 #===END data_(3) _database_code_depnum_ccdc_archive 'CCDC 873665' #TrackingRef '- acrispinirevised.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H24 Ir N4, Cl O4' _chemical_formula_sum 'C28 H24 Cl Ir N4 O4' _chemical_formula_weight 708.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c a 21' _symmetry_space_group_name_Hall 'P 2c -2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 11.0556(10) _cell_length_b 15.2516(15) _cell_length_c 15.3882(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2594.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9973 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 26.79 _exptl_crystal_description parallelepiped _exptl_crystal_colour orange _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.813 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1384 _exptl_absorpt_coefficient_mu 5.291 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.075 _exptl_absorpt_correction_T_max 0.189 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 63126 _diffrn_reflns_av_R_equivalents 0.0403 _diffrn_reflns_av_sigmaI/netI 0.0224 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.34 _diffrn_reflns_theta_max 27.06 _reflns_number_total 5648 _reflns_number_gt 5230 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0216P)^2^+1.2086P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.002(7) _refine_ls_number_reflns 5648 _refine_ls_number_parameters 331 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0214 _refine_ls_R_factor_gt 0.0184 _refine_ls_wR_factor_ref 0.0533 _refine_ls_wR_factor_gt 0.0474 _refine_ls_goodness_of_fit_ref 1.215 _refine_ls_restrained_S_all 1.215 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ir1 Ir 0.049269(9) 0.236736(7) 0.74819(3) 0.03501(5) Uani 1 1 d . . . N1 N 0.1845(3) 0.1697(2) 0.6855(2) 0.0388(7) Uani 1 1 d . . . C1 C 0.2682(5) 0.2067(4) 0.6329(4) 0.0575(13) Uani 1 1 d . . . H1A H 0.2628 0.2663 0.6209 0.069 Uiso 1 1 calc R . . C2 C 0.3619(4) 0.1586(4) 0.5963(4) 0.0690(14) Uani 1 1 d . . . H2A H 0.4183 0.1853 0.5601 0.083 Uiso 1 1 calc R . . C3 C 0.3690(5) 0.0718(4) 0.6145(4) 0.0724(15) Uani 1 1 d . . . H3B H 0.4302 0.0381 0.5898 0.087 Uiso 1 1 calc R . . C4 C 0.2873(4) 0.0338(3) 0.6686(3) 0.0605(12) Uani 1 1 d . . . H4A H 0.2935 -0.0257 0.6814 0.073 Uiso 1 1 calc R . . C5 C 0.1950(3) 0.0829(3) 0.7048(3) 0.0427(9) Uani 1 1 d . . . C6 C 0.1047(4) 0.0515(2) 0.7663(3) 0.0422(11) Uani 1 1 d . . . C7 C 0.0947(5) -0.0351(3) 0.7919(3) 0.0565(11) Uani 1 1 d . . . H7A H 0.1473 -0.0768 0.7691 0.068 Uiso 1 1 calc R . . C8 C 0.0082(5) -0.0599(4) 0.8504(4) 0.0680(14) Uani 1 1 d . . . H8A H 0.0038 -0.1180 0.8684 0.082 Uiso 1 1 calc R . . C9 C -0.0720(5) 0.0004(4) 0.8826(3) 0.0641(13) Uani 1 1 d . . . H9A H -0.1315 -0.0168 0.9218 0.077 Uiso 1 1 calc R . . C10 C -0.0642(4) 0.0874(3) 0.8563(3) 0.0514(11) Uani 1 1 d . . . H10A H -0.1191 0.1279 0.8784 0.062 Uiso 1 1 calc R . . C11 C 0.0243(3) 0.1158(3) 0.7976(3) 0.0377(8) Uani 1 1 d . . . N2 N -0.0929(3) 0.2914(2) 0.8131(2) 0.0434(7) Uani 1 1 d . . . C12 C -0.0865(4) 0.3293(3) 0.8919(3) 0.0516(10) Uani 1 1 d . . . H12A H -0.0116 0.3311 0.9194 0.062 Uiso 1 1 calc R . . C13 C -0.1821(5) 0.3647(3) 0.9335(3) 0.0637(13) Uani 1 1 d . . . H13A H -0.1738 0.3896 0.9883 0.076 Uiso 1 1 calc R . . C14 C -0.2935(5) 0.3628(4) 0.8915(4) 0.0744(16) Uani 1 1 d . . . H14A H -0.3613 0.3871 0.9179 0.089 Uiso 1 1 calc R . . C15 C -0.3027(4) 0.3252(4) 0.8119(4) 0.0693(14) Uani 1 1 d . . . H15A H -0.3769 0.3244 0.7835 0.083 Uiso 1 1 calc R . . C16 C -0.2020(4) 0.2881(3) 0.7725(3) 0.0474(12) Uani 1 1 d . . . C17 C -0.1997(4) 0.2413(3) 0.6887(3) 0.0451(10) Uani 1 1 d . . . C18 C -0.3012(5) 0.2279(4) 0.6385(4) 0.0614(13) Uani 1 1 d . . . H18A H -0.3752 0.2510 0.6561 0.074 Uiso 1 1 calc R . . C19 C -0.2937(4) 0.1805(4) 0.5624(3) 0.0692(15) Uani 1 1 d . . . H19A H -0.3624 0.1707 0.5290 0.083 Uiso 1 1 calc R . . C20 C -0.1825(4) 0.1474(4) 0.5362(3) 0.0600(13) Uani 1 1 d . . . H20A H -0.1768 0.1161 0.4845 0.072 Uiso 1 1 calc R . . C21 C -0.0792(4) 0.1609(3) 0.5868(3) 0.0492(10) Uani 1 1 d . . . H21A H -0.0055 0.1380 0.5685 0.059 Uiso 1 1 calc R . . C22 C -0.0849(3) 0.2089(3) 0.6650(3) 0.0414(9) Uani 1 1 d . . . N3 N 0.0860(3) 0.3682(2) 0.6971(3) 0.0528(9) Uani 1 1 d . . . H3A H 0.1376 0.3648 0.6520 0.063 Uiso 1 1 calc R . . H3C H 0.0169 0.3930 0.6783 0.063 Uiso 1 1 calc R . . C23 C 0.1390(4) 0.4216(3) 0.7664(5) 0.0667(19) Uani 1 1 d . . . H23A H 0.0745 0.4471 0.8009 0.080 Uiso 1 1 calc R . . H23B H 0.1848 0.4692 0.7407 0.080 Uiso 1 1 calc R . . N4 N 0.1883(2) 0.28220(18) 0.83215(18) 0.0475(8) Uani 1 1 d G . . C24 C 0.2188(3) 0.37017(17) 0.8233(2) 0.0601(12) Uani 1 1 d G . . C25 C 0.3145(3) 0.4048(2) 0.8707(3) 0.081(2) Uani 1 1 d G . . H25A H 0.3349 0.4637 0.8648 0.098 Uiso 1 1 calc R . . C26 C 0.3798(3) 0.3515(3) 0.9270(2) 0.093(2) Uani 1 1 d G . . H26A H 0.4438 0.3746 0.9588 0.111 Uiso 1 1 calc R . . C27 C 0.3493(3) 0.2635(3) 0.9359(2) 0.0788(19) Uani 1 1 d G . . H27A H 0.3929 0.2278 0.9735 0.095 Uiso 1 1 calc R . . C28 C 0.2535(3) 0.22887(18) 0.8884(2) 0.0620(17) Uani 1 1 d G . . H28A H 0.2331 0.1700 0.8944 0.074 Uiso 1 1 calc R . . Cl1 Cl 0.09933(13) -0.54462(9) 1.09371(9) 0.0662(3) Uani 1 1 d . . . O1 O 0.0444(5) -0.4983(6) 1.0312(5) 0.164(3) Uani 1 1 d . . . O2 O 0.2130(5) -0.5745(5) 1.0749(4) 0.159(3) Uani 1 1 d . . . O3 O 0.0364(8) -0.6123(9) 1.1164(12) 0.338(11) Uani 1 1 d . . . O4 O 0.1150(9) -0.4944(10) 1.1622(7) 0.345(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ir1 0.02924(6) 0.03015(7) 0.04564(8) 0.0012(2) -0.00071(12) 0.00054(4) N1 0.0314(15) 0.0363(17) 0.0486(18) 0.0024(14) -0.0013(13) 0.0012(13) C1 0.040(2) 0.067(3) 0.065(3) 0.009(3) 0.005(2) -0.003(2) C2 0.050(3) 0.074(4) 0.082(4) 0.006(3) 0.023(3) 0.005(2) C3 0.060(3) 0.073(4) 0.084(4) -0.006(3) 0.017(3) 0.023(3) C4 0.058(3) 0.051(3) 0.072(3) -0.001(2) 0.010(2) 0.016(2) C5 0.0398(19) 0.037(2) 0.051(2) -0.0003(17) -0.0039(17) 0.0053(16) C6 0.0435(18) 0.0343(17) 0.049(3) 0.0009(16) -0.0045(17) 0.0022(14) C7 0.059(3) 0.042(2) 0.069(3) 0.006(2) -0.003(2) 0.005(2) C8 0.074(3) 0.048(3) 0.082(4) 0.024(3) -0.009(3) -0.007(3) C9 0.069(3) 0.058(3) 0.065(3) 0.015(3) 0.008(2) -0.013(3) C10 0.055(2) 0.049(3) 0.051(2) 0.004(2) 0.0044(19) -0.004(2) C11 0.0392(19) 0.033(2) 0.041(2) 0.0046(16) -0.0019(15) -0.0019(15) N2 0.0360(16) 0.0407(18) 0.054(2) 0.0001(16) 0.0050(15) 0.0053(15) C12 0.053(2) 0.044(2) 0.057(3) -0.005(2) 0.003(2) 0.002(2) C13 0.066(3) 0.057(3) 0.068(3) -0.009(2) 0.017(2) 0.005(2) C14 0.050(3) 0.079(4) 0.094(4) -0.018(3) 0.018(3) 0.007(3) C15 0.041(2) 0.072(3) 0.095(4) -0.014(3) 0.010(2) 0.006(2) C16 0.0336(18) 0.044(2) 0.065(4) 0.0018(19) 0.0047(17) 0.0041(17) C17 0.035(2) 0.049(3) 0.052(3) 0.0086(19) -0.0012(19) -0.0020(18) C18 0.037(2) 0.076(4) 0.072(3) 0.009(3) -0.006(2) 0.002(2) C19 0.048(2) 0.101(4) 0.059(3) 0.004(3) -0.014(2) -0.003(3) C20 0.057(3) 0.083(4) 0.041(2) 0.001(2) -0.008(2) -0.014(2) C21 0.042(2) 0.055(3) 0.050(2) 0.004(2) 0.0041(19) -0.0086(19) C22 0.0324(18) 0.041(2) 0.051(2) 0.0084(18) -0.0039(17) -0.0090(17) N3 0.0493(19) 0.0367(19) 0.072(2) 0.0098(18) 0.0079(19) 0.0053(16) C23 0.061(3) 0.0363(19) 0.102(6) -0.006(3) 0.012(3) -0.0058(19) N4 0.0352(17) 0.049(2) 0.058(2) -0.0093(17) -0.0039(16) 0.0033(15) C24 0.041(2) 0.055(3) 0.084(3) -0.019(3) 0.012(2) -0.007(2) C25 0.057(3) 0.083(4) 0.104(5) -0.047(4) 0.011(3) -0.028(3) C26 0.040(3) 0.148(7) 0.090(5) -0.049(5) 0.000(3) -0.001(4) C27 0.051(3) 0.119(6) 0.067(4) -0.032(3) -0.011(3) 0.017(3) C28 0.050(3) 0.080(4) 0.056(3) -0.010(3) -0.016(3) 0.018(3) Cl1 0.0624(7) 0.0604(7) 0.0758(8) -0.0006(6) -0.0029(6) 0.0183(6) O1 0.122(5) 0.176(8) 0.196(7) 0.103(6) -0.018(4) 0.035(4) O2 0.125(4) 0.225(8) 0.128(5) 0.023(5) 0.023(4) 0.111(5) O3 0.197(9) 0.275(15) 0.54(3) 0.264(17) -0.080(12) -0.104(9) O4 0.221(9) 0.49(2) 0.322(13) -0.296(14) -0.147(9) 0.241(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ir1 C22 2.005(4) . ? Ir1 C11 2.014(4) . ? Ir1 N2 2.041(3) . ? Ir1 N1 2.052(3) . ? Ir1 N4 2.124(2) . ? Ir1 N3 2.192(4) . ? N1 C1 1.353(6) . ? N1 C5 1.361(5) . ? C1 C2 1.389(7) . ? C1 H1A 0.9300 . ? C2 C3 1.355(8) . ? C2 H2A 0.9300 . ? C3 C4 1.359(7) . ? C3 H3B 0.9300 . ? C4 C5 1.383(6) . ? C4 H4A 0.9300 . ? C5 C6 1.457(6) . ? C6 C7 1.382(6) . ? C6 C11 1.407(6) . ? C7 C8 1.367(8) . ? C7 H7A 0.9300 . ? C8 C9 1.371(8) . ? C8 H8A 0.9300 . ? C9 C10 1.389(7) . ? C9 H9A 0.9300 . ? C10 C11 1.401(6) . ? C10 H10A 0.9300 . ? N2 C12 1.345(6) . ? N2 C16 1.359(5) . ? C12 C13 1.348(6) . ? C12 H12A 0.9300 . ? C13 C14 1.391(7) . ? C13 H13A 0.9300 . ? C14 C15 1.356(8) . ? C14 H14A 0.9300 . ? C15 C16 1.388(6) . ? C15 H15A 0.9300 . ? C16 C17 1.474(7) . ? C17 C18 1.377(7) . ? C17 C22 1.410(6) . ? C18 C19 1.379(8) . ? C18 H18A 0.9300 . ? C19 C20 1.388(7) . ? C19 H19A 0.9300 . ? C20 C21 1.398(6) . ? C20 H20A 0.9300 . ? C21 C22 1.410(6) . ? C21 H21A 0.9300 . ? N3 C23 1.463(7) . ? N3 H3A 0.9000 . ? N3 H3C 0.9000 . ? C23 C24 1.470(6) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? N4 C24 1.3900 . ? N4 C28 1.3900 . ? C24 C25 1.3900 . ? C25 C26 1.3900 . ? C25 H25A 0.9300 . ? C26 C27 1.3900 . ? C26 H26A 0.9300 . ? C27 C28 1.3900 . ? C27 H27A 0.9300 . ? C28 H28A 0.9300 . ? Cl1 O3 1.293(9) . ? Cl1 O1 1.339(6) . ? Cl1 O2 1.368(5) . ? Cl1 O4 1.314(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C22 Ir1 C11 86.87(16) . . ? C22 Ir1 N2 80.18(17) . . ? C11 Ir1 N2 94.84(15) . . ? C22 Ir1 N1 97.66(16) . . ? C11 Ir1 N1 79.64(14) . . ? N2 Ir1 N1 174.21(14) . . ? C22 Ir1 N4 173.15(14) . . ? C11 Ir1 N4 99.71(13) . . ? N2 Ir1 N4 97.25(14) . . ? N1 Ir1 N4 85.49(12) . . ? C22 Ir1 N3 95.86(16) . . ? C11 Ir1 N3 177.02(14) . . ? N2 Ir1 N3 86.81(15) . . ? N1 Ir1 N3 98.78(14) . . ? N4 Ir1 N3 77.60(13) . . ? C1 N1 C5 118.6(4) . . ? C1 N1 Ir1 124.8(3) . . ? C5 N1 Ir1 116.4(3) . . ? N1 C1 C2 122.2(5) . . ? N1 C1 H1A 118.9 . . ? C2 C1 H1A 118.9 . . ? C3 C2 C1 118.4(5) . . ? C3 C2 H2A 120.8 . . ? C1 C2 H2A 120.8 . . ? C4 C3 C2 120.3(5) . . ? C4 C3 H3B 119.8 . . ? C2 C3 H3B 119.8 . . ? C3 C4 C5 120.4(5) . . ? C3 C4 H4A 119.8 . . ? C5 C4 H4A 119.8 . . ? N1 C5 C4 120.1(4) . . ? N1 C5 C6 113.8(3) . . ? C4 C5 C6 126.1(4) . . ? C7 C6 C11 121.2(4) . . ? C7 C6 C5 123.6(4) . . ? C11 C6 C5 115.2(3) . . ? C8 C7 C6 120.5(5) . . ? C8 C7 H7A 119.8 . . ? C6 C7 H7A 119.8 . . ? C7 C8 C9 120.3(5) . . ? C7 C8 H8A 119.8 . . ? C9 C8 H8A 119.8 . . ? C8 C9 C10 119.7(5) . . ? C8 C9 H9A 120.1 . . ? C10 C9 H9A 120.1 . . ? C11 C10 C9 121.7(5) . . ? C11 C10 H10A 119.1 . . ? C9 C10 H10A 119.1 . . ? C10 C11 C6 116.5(4) . . ? C10 C11 Ir1 128.5(3) . . ? C6 C11 Ir1 115.0(3) . . ? C12 N2 C16 118.6(4) . . ? C12 N2 Ir1 125.2(3) . . ? C16 N2 Ir1 116.3(3) . . ? C13 C12 N2 123.9(5) . . ? C13 C12 H12A 118.0 . . ? N2 C12 H12A 118.0 . . ? C12 C13 C14 117.7(5) . . ? C12 C13 H13A 121.1 . . ? C14 C13 H13A 121.1 . . ? C15 C14 C13 119.7(5) . . ? C15 C14 H14A 120.2 . . ? C13 C14 H14A 120.2 . . ? C14 C15 C16 120.5(5) . . ? C14 C15 H15A 119.8 . . ? C16 C15 H15A 119.8 . . ? N2 C16 C15 119.7(4) . . ? N2 C16 C17 113.9(4) . . ? C15 C16 C17 126.4(4) . . ? C18 C17 C22 122.5(5) . . ? C18 C17 C16 123.2(4) . . ? C22 C17 C16 114.3(4) . . ? C19 C18 C17 120.3(5) . . ? C19 C18 H18A 119.9 . . ? C17 C18 H18A 119.9 . . ? C18 C19 C20 119.4(4) . . ? C18 C19 H19A 120.3 . . ? C20 C19 H19A 120.3 . . ? C19 C20 C21 120.5(5) . . ? C19 C20 H20A 119.7 . . ? C21 C20 H20A 119.7 . . ? C20 C21 C22 121.0(4) . . ? C20 C21 H21A 119.5 . . ? C22 C21 H21A 119.5 . . ? C21 C22 C17 116.3(4) . . ? C21 C22 Ir1 128.5(3) . . ? C17 C22 Ir1 115.2(3) . . ? C23 N3 Ir1 108.7(3) . . ? C23 N3 H3A 109.9 . . ? Ir1 N3 H3A 109.9 . . ? C23 N3 H3C 109.9 . . ? Ir1 N3 H3C 109.9 . . ? H3A N3 H3C 108.3 . . ? N3 C23 C24 112.2(3) . . ? N3 C23 H23A 109.2 . . ? C24 C23 H23A 109.2 . . ? N3 C23 H23B 109.2 . . ? C24 C23 H23B 109.2 . . ? H23A C23 H23B 107.9 . . ? C24 N4 C28 120.0 . . ? C24 N4 Ir1 115.53(16) . . ? C28 N4 Ir1 124.29(16) . . ? C25 C24 N4 120.0 . . ? C25 C24 C23 124.6(3) . . ? N4 C24 C23 115.3(3) . . ? C24 C25 C26 120.0 . . ? C24 C25 H25A 120.0 . . ? C26 C25 H25A 120.0 . . ? C27 C26 C25 120.0 . . ? C27 C26 H26A 120.0 . . ? C25 C26 H26A 120.0 . . ? C28 C27 C26 120.0 . . ? C28 C27 H27A 120.0 . . ? C26 C27 H27A 120.0 . . ? C27 C28 N4 120.0 . . ? C27 C28 H28A 120.0 . . ? N4 C28 H28A 120.0 . . ? O3 Cl1 O1 111.8(6) . . ? O3 Cl1 O2 106.6(7) . . ? O1 Cl1 O2 116.1(4) . . ? O3 Cl1 O4 108.7(10) . . ? O1 Cl1 O4 109.2(7) . . ? O2 Cl1 O4 104.0(5) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3A O2 0.90 2.23 3.039(7) 148.7 3_564 N3 H3C O4 0.90 2.14 2.989(8) 156.7 2_554 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.06 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.725 _refine_diff_density_min -0.348 _refine_diff_density_rms 0.067 #===END